Automated Solution-Phase Synthesis of Oligosaccharides via Iterative Electrochemical Assembly of Thioglycosides

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• 作者：Toshiki Nokami ; Ryutaro Hayashi ; Yoshihiro Saigusa ; Akihiro Shimizu ; Chih-Yueh Liu ; Kwok-Kong Tony Mong ; Jun-ichi Yoshida
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：September 6, 2013
• 年：2013
• 卷：15
• 期：17
• 页码：4520-4523
• 全文大小：302K
• 年卷期：v.15,no.17(September 6, 2013)
• ISSN：1523-7052

文摘

A new iterative one-pot sequential method for the solution-phase synthesis of oligosaccharides has been devised on the basis of the electrochemical oxidation of a propagating thioglycoside terminus to generate the corresponding triflate, followed by the reaction with a thioglycoside building block having a free hydroxyl group. A practical automated synthesizer was developed for the method and was effectively used for assembling up to six thioglycoside building blocks to synthesize partial structures of poly-尾-d-(1鈥?)-N-acetylglucosamine.